tert-Butanol → 4-(1-benzyl-1H-1,2,3-triazol-4-yl)-2-(2-nitro-5-(piperidin-1-yl)phenyl)pyridine

HRID 625315노트

반응식

HRID 625315 반응식
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[C:13]([N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[CH:12]=[CH:11][C:10]=2[N+:21]([O-:23])=[O:22])[CH:4]=1)#[CH:2].[CH2:24]([N:31]=[N+:32]=[N-:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].C(O)(C)(C)C>[O-]S([O-])(=O)=O.[Cu+2].O>[CH2:24]([N:31]1[CH:2]=[C:1]([C:3]2[CH:8]=[CH:7][N:6]=[C:5]([C:9]3[CH:14]=[C:13]([N:15]4[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]4)[CH:12]=[CH:11][C:10]=3[N+:21]([O-:23])=[O:22])[CH:4]=2)[N:33]=[N:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

참가 물질

7

반응물 4

HCID 6386tert-ButanolHCID 12152Benzyl azideHCID 23667548Sodium AscorbateHCID 867059454-Ethynyl-2-(2-nitro-5-(piperidin-1-yl)phenyl)pyridine

생성물 1

HCID 867059464-(1-benzyl-1H-1,2,3-triazol-4-yl)-2-(2-nitro-5-(piperidin-1-yl)phenyl)pyridine

시약·촉매·용매 2

HCID 24462Copper Sulfate촉매HCID 962Water용매

실험 절차

A solution of 50 mg of 4-ethynyl-2-(2-nitro-5-(piperidin-1-yl)phenyl)pyridine, 20 μL of benzyl azide, 16.3 μL of 1 M aqueous sodium ascorbate solution, 5.4 μL of 0.3 M CuSO4 solution, 326 μL of tert-butanol, and 326 μL of water was stirred for 2 days and then the solvent was evaporated at reduced pressure. The residue was dissolved in dichloromethane. The solution was washed with water and dried. The solvent was evaporated at reduced pressure and the residue was chromatographed on silica gel eluting with a 0% to 4% gradient of methanol in dichloromethane. The process yielded 22 mg of product.

후처리

  1. customthe solvent was evaporated at reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washThe solution was washed with water
  4. customdried
  5. customThe solvent was evaporated at reduced pressure
  6. customthe residue was chromatographed on silica gel eluting with a 0% to 4% gradient of methanol in dichloromethane

출처 및 근거

ORD 기록
ord-2a7f511b2b1d495d926d44fda02ea020
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09301951B2

반응 노트

불러오는 중…